Isobutyraldehyde → HCID 57699901, compound

HRID 1686010Notes

Reaction equation

HRID 1686010 reaction equation
[CH:1]1([O:6][C:7](=[O:41])[C@@H:8]([NH2:40])[CH2:9][CH2:10][O:11][C:12]2[CH:21]=[C:20]3[C:15]([C:16]([O:22][C:23]4[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:37])[C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[CH:25][CH:24]=4)=[CH:17][CH:18]=[N:19]3)=[CH:14][C:13]=2[O:38][CH3:39])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:42](=O)[CH:43]([CH3:45])[CH3:44].C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH:1]1([O:6][C:7](=[O:41])[C@@H:8]([NH:40][CH2:42][CH:43]([CH3:45])[CH3:44])[CH2:9][CH2:10][O:11][C:12]2[CH:21]=[C:20]3[C:15]([C:16]([O:22][C:23]4[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:37])[C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)=[CH:25][CH:24]=4)=[CH:17][CH:18]=[N:19]3)=[CH:14][C:13]=2[O:38][CH3:39])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6561IsobutyraldehydeHCID 5003444Sodium cyanoborohydrideHCID 11949608HCID 11949608, compound

Product 1

HCID 57699901HCID 57699901, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent2×

Procedure

To (S)-2-Amino-4-[4-(4-benzoylamino-phenoxy)-6-methoxy-quinolin-7-yloxy]-butyric acid cyclopentyl ester (37 mg, 0.066 mmol) in anhydrous methanol (1 ml) were added 100 μL of a 1 M solution of isobutyraldehyde in methanol and 1 drop of acetic acid. The reaction mixture was stirred at room temperature for 3 hours. Sodium cyanoborohydride (10.3 mg, 0.165 mmol) was then added and the reaction was left stirring 4 hours at room temperature, prior to concentration under vacuum. Purification by preparative HPLC afforded the title compound as a di-TFA salt (40 mg, 72% yield).

Workup

  1. waitthe reaction was left
  2. stirringstirring 4 hours at room temperature
  3. concentrationto concentration under vacuum
  4. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-c37a9f299a244ed0854de78e158c0cf6
Source dataset
uspto-grants-2012_04
Patent number
US08148531B2

Reaction notes

Loading…